4-Bromobenzyl bromide → 4-(4-Bromophenyl)-1-butene

A 250 ml two-necked round-bottom flask, equipped with an additional funnel and condenser, was charged with 4-bromo-benzyl bromide (20.0 g, 80 mmol) in 50 ml dry ether at 0° C. ice bath for 10 min. The allylmagnesium chloride (48.0 ml of a 2.0 M solution in ether, 96 mmol) was added dropwisely via an additional funnel over a period of 30 min at 0° C. Subsequently, the mixture was stirred at room temperature for 2 h and refluxed for another 3 h. The reaction was monitored by TLC analysis. After the starting material disappeared, the reaction was quenched by water and transferred to a separation funnel. The organic layer was washed with brine, dried over anhydrous MgSO4, and then concentrated under vacuum to yield a yellow crude liquid. The product was purified by Kugelrhor distillation to obtain the final product as a transparent liquid (14.10 g, 83%), whose 1H and 13C NMR spectra matched with the earlier reported literature data [7].

1. customA 250 ml two-necked round-bottom flask, equipped with an additional funnel and condenser
2. temperaturerefluxed for another 3 h
3. customthe reaction was quenched by water
4. customtransferred to a separation funnel
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated under vacuum
8. customto yield a yellow crude liquid
9. distillationThe product was purified by Kugelrhor distillation

ORD record

ord-b94fbc8ccf2b4063aa57bc48fa7d4a27

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993793B1